Iodine → Silafluofen

HRID 247659

Reaction equation

HRID 247659 reaction equation
II.Br[CH2:4][CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][C:10]([F:13])=[C:9]([O:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:8]=1.[Mg].Cl[Si:23]([C:26]1[CH:31]=[CH:30][C:29]([O:32][CH2:33][CH3:34])=[CH:28][CH:27]=1)([CH3:25])[CH3:24]>O1CCCC1.C(OCC)C>[CH2:33]([O:32][C:29]1[CH:30]=[CH:31][C:26]([Si:23]([CH2:4][CH2:5][CH2:6][C:7]2[CH:12]=[CH:11][C:10]([F:13])=[C:9]([O:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[CH:8]=2)([CH3:24])[CH3:25])=[CH:27][CH:28]=1)[CH3:34]

Participants

7

Reactant 4

HCID 807IodineHCID 5462224MagnesiumHCID 11781825Benzene, 4-(3-bromopropyl)-1-fluoro-2-phenoxy-HCID 14014482Chloro(4-ethoxyphenyl)dimethylsilane

Product 1

HCID 92430Silafluofen

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
10 °C

Procedure

A small crystal of iodine was added to a mixture of 0.75 g (0.0024 mole) of 1-bromo-3-(4-fluoro-3-phenoxyphenyl)propane and 0.11 g (0.0045 mole) of magnesium powder in 1 ml of tetrahydrofuran. This mixture was heated in a water bath for about three hours. After heating, the clear solution was light grey-brown in color. The solution was cooled to 10° C., and 0.51 g (0.0022 mole) of chloro(4-ethoxyphenyl)dimethylsilane was added. This mixture was stirred for one-half hour and was then heated for an hour. Following dilution with diethyl ether, the reaction mixture was washed successively with 10% hydrochloric acid and a saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under reduced pressure, leaving a colorless oil weighing 0.95 g as the residue. This oil was purified using a Chromatotron (eluant=ethyl acetate/hexane (2:98)), producing (4-ethoxyphenyl)[3-(4-fluoro-3-phenoxyphenyl)propyl]dimethylsilane as a colorless oil. The proton and 13C nmr spectra were consistent with the proposed structure.

Workup

  1. temperatureThis mixture was heated in a water bath for about three hours
  2. temperatureAfter heating
  3. temperaturewas then heated for an hour
  4. washthe reaction mixture was washed successively with 10% hydrochloric acid
  5. dry with materiala saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated under reduced pressure
  8. customleaving a colorless oil
  9. customThis oil was purified

Sources & evidence

ORD record
ord-80c3c0f2de454f139919488c3c15e12a
Source dataset
uspto-grants-1987_11
Patent number
US04709068

Linked notes

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